In this episode of Estate Planning Nightmares… and How to Avoid Them, host Jon Braddock welcomes Holly Simpson — attorney, law firm founder, former therapist, and the driving force behind Simpson Law Firm in Fort Mill, South Carolina.

What began as a solo journey just seven years ago has grown into a thriving estate planning practice with a team of 32 — built not through overnight success, but through Holly’s powerful philosophy of improving just 1% every day in every corner of the business. From legal processes to client experience, that small-step mindset has been a game changer.

Holly shares how her background in therapy helps her connect with families on a deeper level, and how the firm’s Southern-style hospitality — which starts the moment you’re greeted by their receptionist — sets the tone for an experience that’s as warm and welcoming as it is professional.

We’ll explore:

• The biggest estate planning mistakes families make (and how to avoid them)

• Why Holly believes planning is just the beginning of the relationship

• What it takes to build a client-first culture in a law firm

• How one simple value — call clients back — became a differentiator

• And how 80s music, pickleball, mentoring teens, and being a “Grandma” all fit into her story

This episode is packed with real-life insight and inspiration for anyone looking to make estate planning more human — and more effective.

Connect with Holly Here:

Simpson Law Firm

Website:

https://simpsonestatelaw.com/

Facebook:

https://www.facebook.com/SimpsonLawFirmCarolina

Instagram:

https://www.instagram.com/simpsonlawfirm/

LinkedIn:

https://www.linkedin.com/company/simpsonlawfirm/about/